反应详情

温度

90 °C

To a stirred suspension of 2-bromo-3-methoxycyclopent-2-enone (17.5 g, 91.6 mmol), 2,6-diethyl-4-methylphenyl boronic acid (26.4 g, 137 mmol) and freshly powdered potassium phosphate (38.9 g, 183 mmol) in anhydrous, degassed toluene (450 ml) under a nitrogen atmosphere are added palladium (II)acetate (0.411 g, 1.83 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.51 g, 3.67 mmol). The reaction mixture is heated at 90° C. for 6.5 hours and then allowed to cool to room temperature overnight. The reaction is diluted with water (400 ml) and extracted with ethyl acetate (3×150 ml). The combined organic extracts are washed with brine (50 ml), dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated to dryness under reduced pressure to give a brown oil. The crude product is purified by column chromatography on silica gel to give 2-(2,6-diethyl-4-methylphenyl)-3-methoxycyclopent-2-enone.

1. customdegassed toluene (450 ml) under a nitrogen atmosphere
2. temperatureto cool to room temperature overnight
3. extractionextracted with ethyl acetate (3×150 ml)
4. washThe combined organic extracts are washed with brine (50 ml)
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. customthe filtrate is evaporated to dryness under reduced pressure
8. customto give a brown oil
9. customThe crude product is purified by column chromatography on silica gel